Methane → 3-(5-Chloro-2-methoxybenzamido)-2,2-dimethyl-6-(methylaminocarbonylaminosulfonyl)-7-methoxychroman

HRID 1457755Notes

Reaction equation

HRID 1457755 reaction equation
[CH3:1][NH:2][C:3](=[O:8])C(Cl)(Cl)Cl.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:37][CH3:38])=[C:14]([CH:36]=1)[C:15]([NH:17][CH:18]1[CH2:27][C:26]2[C:21](=[CH:22][C:23]([O:32][CH3:33])=[C:24]([S:28](=[O:31])(=[O:30])[NH2:29])[CH:25]=2)[O:20][C:19]1([CH3:35])[CH3:34])=[O:16].[OH-].[Na+].C>>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:37][CH3:38])=[C:14]([CH:36]=1)[C:15]([NH:17][CH:18]1[CH2:27][C:26]2[C:21](=[CH:22][C:23]([O:32][CH3:33])=[C:24]([S:28]([NH:29][C:3]([NH:2][CH3:1])=[O:8])(=[O:30])=[O:31])[CH:25]=2)[O:20][C:19]1([CH3:35])[CH3:34])=[O:16]

Participants

5

Reactant 4

HCID 297MethaneHCID 14798Sodium HydroxideHCID 2486522,2,2-Trichloro-n-methylacetamideHCID 221004413-(5-Chloro-2-methoxybenzamido)-2,2-dimethyl-6-sulfamoyl-7-methoxychroman

Product 1

HCID 221004703-(5-Chloro-2-methoxybenzamido)-2,2-dimethyl-6-(methylaminocarbonylaminosulfonyl)-7-methoxychroman

Conditions

Temperature
80 °C

Procedure

1.23 g (7.5 mmol) of N-methyltrichloroacetamide were added to 2.27 g (5 mmol) of 3-(5-chloro-2-methoxybenzamido)-2,2-dimethyl-6-sulfamoyl-7-methoxychroman and 0.5 g (12.5 mmol) of finely powdered sodium hydroxide. After the mixture had been stirred at 80° C. for half an hour, it was introduced into ice/water, clarified with charcoal and acidified to pH 1. The precipitate was filtered off with suction, dried and recrystallized from ethanol/DMF. The product had a melting point of 248° C.

Workup

  1. filtrationThe precipitate was filtered off with suction
  2. customdried
  3. customrecrystallized from ethanol/DMF

Sources & evidence

ORD record
ord-16eecf5dd5c2493bb7c0041507458fe4
Source dataset
uspto-grants-1998_12
Patent number
US05849755

Reaction notes

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